Holiday rentals with a kayak in Kaanapali

A round glass-topped dining table is set on a private lanai, accompanied by comfortable wicker chairs. A bottle of wine and glasses are artfully arranged on a wooden tray, with sweeping ocean views extending towards distant islands under a bright sky.

4.94 out of 5 average rating, 145 reviews

Maui Beachfront Oceanfront Sands of Kahana withA/C

Mar 10 -Mar 14 OPEN! 🌺 Ocean and Beachfront views at Sands of Kahana with ❄️Air Conditioning! 🏖️ Escape to Maui, Hawaii! Ocean/Beachfront Resort with onsite dining at Captain Jacks. This 5-star spacious 2 bed 2 bath condo offers breathtaking views, stunning sunsets over Molokai & Lanai. Enjoy whale 🐋 and turtle 🐢 watching, surfing 🏄‍♂️, and strolls along the sandy beach. Unwind with warm tropical breezes and libations 🥂 on the lanai. Enjoy the amenities 2 pools, 2 gyms, and Pickleball.

Outdoor spacesLocationWalkability

Top Guest favourite

Apartment in Kaanapali

Direct Oceanfront View at Mahana Studio, King Bed

Welcome to my hotel-zoned oceanfront, direct ocean view studio Enjoy stunning floor-to-ceiling ocean views and breathtaking sunsets over the neighboring islands. See and hear the ocean from your bed and private lanai Featuring a king Murphy bed with a true king size mattress, central AC, smart TV, fast Wi-Fi, fully equipped kitchen, in-unit laundry Free on-site parking, 1 space No resort fees, no other additional fees Oceanfront, direct ocean view on the 4th floor of the Mahana at Ka'anapali

Outdoor spacesLocationQuiet

5.0 out of 5 average rating, 33 reviews

5.0 out of 5 average rating, 7 reviews

A spacious king bed is framed by light blue walls, with decorative accents above the headboard. Large glass doors open to a private lanai offering views of palm trees and the beach. Two bedside lamps provide soft lighting, enhancing the serene atmosphere.

Apartment in Wailea

Oceanfront Dream 2Bed/2Bath-Mana Kai Maui Resort

Incredible location on Keawakapu Beach, the condo views beach & outer islands & has serene villa-like aesthetic with efficient design combining function and comfort! Enjoy dining on the private lanai or in the well-equipped kitchen w/island! Fine finishes, towels, linens, tasteful furnishings and decor make this the perfect choice! King Bed suite is OPEN to living space. WiFi. Smart tv. FREE Parking, Lounges, BBQs, pool, deli+store, fitness gym office, activity desk, 4 beach chairs+bch towels.

LocationOutdoor spacesFamily

A private lanai features a round table surrounded by a light-colored chair. A bottle of champagne and two glasses rest on the table, with flower petals artistically arranged nearby. Lush green grass extends to the beach beyond, complemented by tropical decor in the background.

4.98 out of 5 average rating, 45 reviews

Aloha Aku Bamboo Suite – Discover Beachfront Seren

Our luxury Beachfront estate has 4 beachfront one-bedroom suites and a garden view two-bedroom Ohana. Each suite has a private entrance, separate living room, full kitchen and is like having your own condo at the beach in Maui. This special place is hidden behind a private, double gated entrance, lined with 700 ft of lighted coconut palms that lure you into the feeling of leaving the world behind. But is still centrally placed in Kihei nearly all of the amenities you might desire. BBKM 2013/0002

LocationValueSleep quality

5.0 out of 5 average rating, 6 reviews

Ocean views & ac! - RK602 - Sullivan Properties

This fully renovated studio offers everything you need for a fantastic Maui vacation! Located in the charming town of Kahana this phenomenal resort styled complex includes a wide range of amenities: an Ocean Front Heated Pool, Fitness Center, Free High Speed Internet (Wi-Fi) and Beachfront Access (seasonal). Rental points: Studio (King & Queen Sofa Sleeper), central air-conditioning, Ocean View, Fully Equipped Kitchen, Washer/Dryer in unit, 431 sq. ft, 43” flat-screen TV with cable, Elevator,

LocationOutdoor spacesCleanliness

A spacious single-story home is surrounded by lush palm trees and vibrant tropical plants. The well-maintained lawn features a mix of greenery, with the house's exterior displaying a neutral tone under a bright blue sky.

4.86 out of 5 average rating, 174 reviews

Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01

WONDERFUL! Three bedroom hale (home) in the Central Kihei area of Maui. Wood floors, lots of space, kitchen fully stocked, BBQ and so much more. Great for kids, elderly, and young at heart. This house is your home away from home. We have all of the necessary items for a home. If we do not have something please let us know and we will try our best to accommodated. Walking distance to the beach, shopping, park, public transportation, etc... You will not find a better place in Kihei.

ValueLocationBackyard

An outdoor dining area is displayed on a balcony, showcasing a table set for four. The picturesque beach and calm ocean waters extend in the background under a partly cloudy sky, enhancing the inviting atmosphere for al fresco dining.

4.95 out of 5 average rating, 113 reviews

Direct Beachfront A/C & on Sandy Swimmable Beach

Zoned "Hotel/Resort" so no need to worry about our zoning. 8th floor unit on a sandy swimmable beach with A/C. Perfect location for watching the beautiful sunsets, see our resident sea turtles and an excellent place for spotting whales during the whale migration season. Beach towels, boogie boards, 4 beach chairs, cooler and much more... Kiddie pool, family pool, pickle ball courts, tennis courts, 2 gyms. Washer/dryer inside the unit. Fully stocked kitchen. Pak n play & highchair.

LocationValueParking

4.9 out of 5 average rating, 21 reviews

Condo in Wailea

Endless Ocean Views - 1bd/2 bath

Experience island living at its finest in this beautiful 1-bedroom, 2-bathroom condo located in the heart of Wailea/Kihei, Hawaii. This serene retreat offers breathtaking ocean views and a peaceful atmosphere, perfect for unwinding after a day of exploring. Just a short stroll from world-renowned beaches and minutes from top-rated shopping, dining, and entertainment, the location couldn’t be more ideal. This well-appointed space is designed for comfort and relaxation.

Outdoor spacesLocationNearby

4.96 out of 5 average rating, 167 reviews

Condo in Kihei

Tropical Retreat • King • Beach • Pool/Hot Tub

Newly remodeled Maui retreat with a plush king bed, designer finishes, and a fully updated kitchen with stainless steel appliances. Bright, open layout with AC and a queen sleeper for added space. Step onto your private lanai overlooking lush tropical gardens, or unwind at the resort’s heated saltwater pool and jacuzzi. Professionally cleaned and thoughtfully stocked - perfect for relaxing, easy island living just moments from the beach.

LocationOutdoor spacesCheckout

A sweeping view of the coastline showcases gently curved sandy beach bordered by lush palms. The turquoise water sparkles under a bright blue sky, while distant mountains are visible along the horizon, creating a serene oceanfront scene.

4.94 out of 5 average rating, 133 reviews

Fantastic Ocean & Island Views!

Welcome to our ocean front dream retreat in Maui, where your senses are filled with the sights and sounds of azure waves and gentle breezes whispering through the palm trees. As soon as you enter through the door of our tropical abode, you'll be greeted by a symphony of light and space, where every corner radiates a welcoming coziness, and beautiful views of the ocean, marine wildlife, and the neighboring islands.

ValueOutdoor spacesQuiet

Top Guest favourite

Condo in Kihei

King Bed + Pools | Steps to Kamaole Beach

Wake up to ocean breezes and unwind with Maui sunsets from your private top-floor lanai. Just steps from Kamaole Beach Park II, this beautifully remodeled retreat features peekaboo ocean views, a plush king bed, resort-style pools and hot tubs, complimentary beach gear, and a prime South Kihei location within walking distance of beaches, dining, and shopping.

ValueOutdoor spacesBarbecue

4.96 out of 5 average rating, 238 reviews

4.83 out of 5 average rating, 94 reviews

Condo in Wailea

Last Minute Deal! Oceanview! 2 Bed 2 Bath LOFT!

Centrally located in the heart of South Kihei, this stunning fourth floor 818 square foot 'loft style' condo with spiral staircase boasts a gorgeous ocean view from the lanai and a very spacious floor plan! The resort like amenities are the one of the finest in all of Kihei!

ValueLocationCheckout

Popular amenities for Kaanapali kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.89 out of 5 average rating, 54 reviews

An open living area features a combination of comfortable seating arrangements, including a green sofa and rattan chairs. Large glass doors lead to a lush garden, while light-colored beams enhance the airy feel. A coffee table sits at the center, adorned with fresh flowers.

Home in Paia

Beach house for wind-sports in Pa’ia-North Shore

LocationOutdoor spacesAccuracy

A spacious sleeping area features a canopy bed adorned with soft bedding, complemented by a tasteful patterned cover. A television is positioned on a low console cabinet opposite the bed, while a closet with hangers is visible in the background. The room is painted in a light blue hue.

Private room in Wailuku

Serene Blue Retreat•Queen Bed•Smart TV•MiniFridge

LocationHospitalityAccuracy

4.57 out of 5 average rating, 7 reviews

An open-concept kitchen and living area features a counter with seating for four, complemented by a wooden dining table for four. Sunlight floods through large sliding glass doors, illuminating stylish furnishings and a lush green lawn visible through the patio area.

4.9 out of 5 average rating, 94 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

Outdoor spacesLocationParking

A winding driveway bordered by lush tropical plants and palm trees leads to the entrance of the estate. The pathway is well-maintained, with bright blue skies overhead and a sense of tranquility inviting guests toward the property.

4.88 out of 5 average rating, 16 reviews

Aloha Aku Ohana Suite – Spacious Garden View Oasis

Outdoor spacesLocationHot tub

A patio area features a light-colored chair and a round table, overlooking a grassy lawn that leads to the ocean. A tree with twisted branches is visible in the background, along with several upright, leafy plants. The inviting blue water of a pool can be seen beneath the sunlit sky.

4.92 out of 5 average rating, 26 reviews

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

LocationOutdoor spacesIndoor spaces

A serene outdoor area includes smooth stone dipping pools and a Jacuzzi with sunset views. Tropical plants are situated in decorative pots, complementing the landscape. The setting is enhanced by tiki torches, and a lush lawn extends towards the horizon under a soft evening sky.

5.0 out of 5 average rating, 7 reviews

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

LocationBreakfastSleep quality

A peaceful outdoor water feature is surrounded by lush palm plants in decorative pots. Water flows gently from stone elements into a serene pool, with a backdrop of green grass and distant mountains. The setting evokes a sense of tranquility and connection with nature.

4.93 out of 5 average rating, 29 reviews

Aloha Aku Honu Suite – Experience the Spirit of Al

LocationOutdoor spacesNearby

A serene view features two carved wooden tiki figures positioned amidst a lush green lawn, leading towards a sparkling blue ocean in the background. Delicate orange flowers are visible in the foreground, adding a touch of color to the tranquil landscape.

5.0 out of 5 average rating, 19 reviews

Aloha Aku CoCoPalm2 Suite – Cozy Beachfront Escape

LocationQuietAccess

Other holiday rentals with a kayak

4.94 out of 5 average rating, 18 reviews

A private lanai is furnished with a small table and two wicker chairs. A fruit platter, featuring bananas, grapes, and a pineapple, is arranged at the center. Lush palm trees and an ocean view complete the inviting outdoor space.

Condo in Kihei

Ocean View Condo in the Heart of Kihei!

LocationViewHospitality

5.0 out of 5 average rating, 3 reviews

Marriott's Maui Ocean Club Resort!

LocationViewBathroom

4.67 out of 5 average rating, 3 reviews

Apartment in Kihei

Oceanfront Kealia 403 Stunning Ocean Views 4th Flr

LocationOutdoor spacesKitchen

A spacious bedroom features a large bed dressed in a light blue quilt, complemented by decorative pillows. Two bedside lamps illuminate the room, while sliding glass doors provide views of the surrounding lush greenery and mountains. A decorative tray with cups and flowers rests on the bed.

4.88 out of 5 average rating, 140 reviews

Beautiful Views~

Outdoor spacesValueQuiet

4.89 out of 5 average rating, 183 reviews

Check In, Chill Out - Annie’s Surf Shack Awaits!

LocationValueBathroom

An elegant dining area is set on a spacious lanai, featuring a table for four adorned with a bouquet of flowers. The background showcases panoramic views of the lush West Maui mountains under a clear blue sky, creating a serene outdoor dining experience.

4.86 out of 5 average rating, 7 reviews

Honua Kai Mountain View 1 BR | 832 by KBM

LocationPoolFamily

Apartment in Napili-Honokowai

Beachfront • Pool + Hot Tub • Pickleball, Tennis

LocationComfortHospitality

4.67 out of 5 average rating, 3 reviews

A bright living area is furnished with a comfortable blue sofa and two armchairs with floral patterns. A large abstract artwork hangs above the sofa, while sliding glass doors open to a view of greenery and mountains. A neutral area rug adds warmth to the hardwood floor.